Stereospecific nucleophilic substitution was achieved for the first time with arylboronic acids as nucleophiles. This transition-metal-free coupling between chiral α-aryl-α-mesylated acetamides and arylboronic acids provided access to a series of chiral α,α-diaryl acetamides with excellent enantioselectivity and moderate to good yields. The CONH functionality proved to be crucial for bridging the reactants and promoting the reaction. Efficient syntheses of a cannabinoid CB receptor ligand, the antidepressant (S)-diclofensine, and a key chiral building block of the inhibitor implitapide were successfully accomplished by using this method.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/anie.201712829 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Nickel-Catalyzed Cyclization/Carbonylation Reaction of -Allylbromoacetamides with Arylboronic Acids toward 2-Pyrrolidinones.
Org Lett
January 2025
Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 116023 Dalian, Liaoning, People's Republic of China.
A straightforward and efficient nickel-catalyzed cyclization/carbonylation transformation of -allylbromoacetamides toward the synthesis of 2-pyrrolidinone derivatives has been developed with arylboronic acids as the reaction partner. This transformation proceeds through a sequential single-electron-transfer pathway via 5-- cyclization and carbonyl insertion steps, furnishing a variety of 2-pyrrolidinone derivatives in good yields. Various useful functional groups were well tolerated.
View Article and Find Full Text PDFNickel-catalyzed cross-coupling of 2-fluorobenzofurans with arylboronic acids via aromatic C-F bond activation.
Beilstein J Org Chem
January 2025
Sagami Chemical Research Institute, 2743-1 Hayakawa, Ayase, Kanagawa 252-1193, Japan.
2-Fluorobenzofurans underwent efficient nickel-catalyzed coupling with arylboronic acids through the activation of aromatic C-F bonds. This method allowed us to successfully synthesize a range of 2-arylbenzofurans with various substituents. The reaction, which proceeded under mild conditions, involved β-fluorine elimination from nickelacyclopropanes formed by the interaction of 2-fluorobenzofurans with zero-valent nickel species.
View Article and Find Full Text PDFMechanochemical Palladium-catalyzed Cross-coupling of Thianthrenium Salts and Arylboronic Acids.
ChemSusChem
January 2025
Comenius University FNS: Univerzita Komenskeho v Bratislave Prirodovedecka fakulta, Organic chemistry, Mlynska dolina, Ilkovicova 6, 84215, Bratislava, SLOVAKIA.
Cross-coupling reactions are indispensable for the construction of complex molecular scaffolds. In this work, we developed a sustainable methodology for the cross-coupling reaction of arene thianthrenium salts with aryl boronic acids, which can be effectively realized under mechanochemical conditions. Liquid-assisted grinding (LAG) enabled fast and high-yielding synthesis of a range of biaryls via Pd/RuPhos-catalyzed cross-coupling.
View Article and Find Full Text PDFCombinatorial Synthesis of Tetrasubstituted Alkenes and Related Compounds with Potential Anticancer Activity.
Comb Chem High Throughput Screen
January 2025
APIGENEX s.r.o., Poděbradská 173/5, Prague 19000, Czech Republic.
Objective: In search of efficient anticancer agents, we aimed at the design and synthesis of a library of tetrasubstituted alkenes. These are structural analogues of tamoxifen, one of the widely used anticancer therapeutics.
Methods: Our small organic compound library was prepared via a chemical synthesis in the solution using the Larock three-component coupling reaction, which is known to tolerate diverse functional groups.
Regio- and Enantioselective Rhodium-Catalyzed Allylic Arylation of Racemic Allylic Carbonates with Arylboronic Acids.
Angew Chem Int Ed Engl
January 2025
New Cornerstone Science Laboratory, State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
Rhodium-catalyzed regio- and enantioselective allylic arylation of racemic alkyl- and aryl- substituted allylic carbonates with arylboronic acids using commercially available BIBOP ligand is reported. This reaction proceeds at room temperature without base or other additive to deliver allylic arylation products in excellent yields, regio- and enantioselectivity (up to 95 % yield, >20 : 1 b/l, >99 % ee). Rh/BIBOP is disclosed as an efficient catalytic system for allylic substitution reaction.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!